CN110386923A - Carbazole compound and its application and organic electroluminescence device - Google Patents
Carbazole compound and its application and organic electroluminescence device Download PDFInfo
- Publication number
- CN110386923A CN110386923A CN201810356462.5A CN201810356462A CN110386923A CN 110386923 A CN110386923 A CN 110386923A CN 201810356462 A CN201810356462 A CN 201810356462A CN 110386923 A CN110386923 A CN 110386923A
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- substituted
- unsubstituted
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- carbazole compound
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- -1 Carbazole compound Chemical class 0.000 title claims abstract description 92
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 title claims abstract description 48
- 238000005401 electroluminescence Methods 0.000 title claims abstract description 38
- 239000000463 material Substances 0.000 claims abstract description 45
- 238000002347 injection Methods 0.000 claims abstract description 11
- 239000007924 injection Substances 0.000 claims abstract description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 33
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- 230000005540 biological transmission Effects 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 7
- 238000006467 substitution reaction Methods 0.000 claims description 7
- 239000000758 substrate Substances 0.000 claims description 7
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 4
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 3
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 125000001725 pyrenyl group Chemical group 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 2
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 2
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 2
- DHFABSXGNHDNCO-UHFFFAOYSA-N dibenzoselenophene Chemical compound C1=CC=C2C3=CC=CC=C3[se]C2=C1 DHFABSXGNHDNCO-UHFFFAOYSA-N 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 claims description 2
- 229960005544 indolocarbazole Drugs 0.000 claims description 2
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 claims description 2
- 125000006610 n-decyloxy group Chemical group 0.000 claims description 2
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 2
- 125000006608 n-octyloxy group Chemical group 0.000 claims description 2
- 150000005054 naphthyridines Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 150000004866 oxadiazoles Chemical class 0.000 claims description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000005580 triphenylene group Chemical group 0.000 claims description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 2
- OGNZZTLIIQCYCG-UHFFFAOYSA-N N1C=CC=CC=C1.C1=CC=CC=2OC3=C(C21)C=CC=C3 Chemical group N1C=CC=CC=C1.C1=CC=CC=2OC3=C(C21)C=CC=C3 OGNZZTLIIQCYCG-UHFFFAOYSA-N 0.000 claims 1
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 150000001716 carbazoles Chemical class 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 57
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract description 18
- 229930192474 thiophene Natural products 0.000 abstract description 9
- 206010011224 Cough Diseases 0.000 abstract description 5
- 238000004220 aggregation Methods 0.000 abstract description 3
- 230000002776 aggregation Effects 0.000 abstract description 3
- 230000006798 recombination Effects 0.000 abstract description 3
- 238000005215 recombination Methods 0.000 abstract description 3
- 150000002220 fluorenes Chemical class 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 78
- 239000000047 product Substances 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 16
- 239000007787 solid Substances 0.000 description 15
- 238000004458 analytical method Methods 0.000 description 14
- 238000010183 spectrum analysis Methods 0.000 description 13
- 150000001793 charged compounds Chemical class 0.000 description 12
- 238000010189 synthetic method Methods 0.000 description 12
- 239000000470 constituent Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- 230000027756 respiratory electron transport chain Effects 0.000 description 9
- 239000000975 dye Substances 0.000 description 8
- 238000007738 vacuum evaporation Methods 0.000 description 8
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 230000003111 delayed effect Effects 0.000 description 4
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- 239000007850 fluorescent dye Substances 0.000 description 4
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 4
- 238000007725 thermal activation Methods 0.000 description 4
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
- 239000004327 boric acid Substances 0.000 description 3
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
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- 150000000182 1,3,5-triazines Chemical class 0.000 description 2
- OTEKOJQFKOIXMU-UHFFFAOYSA-N 1,4-bis(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=C(C(Cl)(Cl)Cl)C=C1 OTEKOJQFKOIXMU-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 150000002739 metals Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N monofluoromethane Natural products FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
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- C07D209/82—Carbazoles; Hydrogenated carbazoles
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Abstract
This disclosure relates to a kind of carbazole compound and its application and organic electroluminescence device, which has structure shown in following general formula (1):
Description
Technical field
This disclosure relates to field of organic electroluminescent materials, and in particular, to a kind of carbazole compound and its application and
Organic electroluminescence device.
Background technique
Since scientist Deng Qingyun of Chinese origin teaches and reported double-deck organic electroluminescence device for the first time in 1987,
Organic electroluminescent LED due to it is ultra-thin, can it is flexible, light-weight, low energy consumption, actively shine, that visual angle is wide, response is fast etc. is many
Advantage has great application prospect in display and lighting area, causes everybody extensive concern, more and more OLED are shown
Start to move towards market with illuminating product.
Traditional fluorescent material can only be carried out luminous using 25% singlet exciton, and luminous efficiency is lower.With phosphorescence
The appearance of material and thermal activation delayed fluorescence material, triplet excitons are utilized, and internal quantum efficiency theoretically may be implemented
100% utilization, external quantum efficiency significantly improve.The excitation purity of luminescent material, efficiency, service life directly affect organic electroluminescence hair
The performance of optical device.Current electroluminescent device luminescent layer uses host-guest system mode mainly to adjust its photochromic, brightness
With efficiency.
Since common material of main part mostly has wider band gap and has unipolar transmission characteristic, exciton note is often led to
Enter obstacle, cut-in voltage is higher.Further, since carrier transport is uneven, causes exciton to meet region and occur under high voltages
Deviate, causes the change and serious efficiency roll-off problem of luminescent spectrum.
Summary of the invention
The purpose of the disclosure is the driving voltage for reducing organic electroluminescence device, improves luminous efficiency.
To achieve the goals above, disclosure first aspect provides a kind of carbazole compound, carbazole compound tool
Just like structure shown in following formula (1):
Wherein, R1、R2、R3And R4In at least one be group shown in formula (2), remaining is selected from hydrogen atom, C1~C10Alkane
Base, substituted or unsubstituted C6~C30Aryl and substituted or unsubstituted C3~C30At least one of heteroaryl；R1’、R2’、R3’
And R4’In at least one be group shown in formula (2), remaining is selected from hydrogen atom, C1~C10Alkyl, substituted or unsubstituted C6~
C30Aryl and substituted or unsubstituted C3~C30At least one of heteroaryl；L is selected from singly-bound, substituted or unsubstituted C6~C30
Arlydene, substituted or unsubstituted C3~C30Inferior heteroaryl；Ar is the group that Hammett value is positive；
Wherein, * is connection site, and X is C atom or Si atom, R5、R6、R7、R8、R5’、R6’、R7’、R8’、R9、R10、R11、
R12And R13It is each independently selected from hydrogen atom, C1~C10Alkyl, substituted or unsubstituted C6~C30Aryl and substituted or unsubstituted
C3~C30At least one of heteroaryl；
The substituted C6~C30Arlydene, substituted C3~C30Inferior heteroaryl, substituted C6~C30Aryl, substituted C3
~C30Substituent group in heteroaryl is each independently selected from halogen, cyano, C1~C10Alkyl, C3~C10Naphthenic base, C2~
C6Alkenyl, C1~C6Alkoxy, C1~C6Thio alkoxy, C6~C30Aryl and C3~C30Heteroaryl at least
It is a kind of.
Disclosure second aspect provides carbazole compound described in disclosure first aspect and is preparing organic electroluminescent
Application in device.
The disclosure third aspect provides a kind of organic electroluminescence device, including substrate, anode layer, cathode layer, Yi Jijie
At least one layer of organic function layer between anode layer and cathode layer, the organic function layer include hole injection layer, hole biography
Defeated layer, organic luminous layer, electron transfer layer and electron injecting layer, the organic function layer contain carbazole described in first aspect
Class compound.
In the carbazole compound of the disclosure, fluorenes, thiophene are coughed up and carbazole group all has preferable cavity transmission ability, when
After introducing the group that the Hammetts values such as pyrimidine, 1,3,5-triazines, carbonyl are positive, the electron-transport energy of molecule can be increased substantially
Power can expand the recombination region of its carrier, be effectively reduced effect when using in the luminescent layer of organic electroluminescence device
Rate is roll-offed；Fluorenes, thiophene are coughed up and carbazole group triplet with higher, can be as three kinds of luminescent materials of red, green, blue
Material of main part uses, in addition, the energy gap of the series compound is also relatively narrow, is conducive to the injection of carrier, can be effectively reduced
The cut-in voltage of device；The compound of the disclosure is connected with fluorenes/thiophene on carbazole and coughs up structure simultaneously, and entire molecule shows larger
Rigid distortion structure, can be effectively reduced because aggregation caused by be quenched, the luminous effect of organic electroluminescence device can be improved
Rate.
Other feature and advantage of the disclosure will the following detailed description will be given in the detailed implementation section.
Specific embodiment
The specific embodiment of the disclosure is described in detail below.It should be understood that described herein specific
Embodiment is only used for describing and explaining the disclosure, is not limited to the disclosure.
Disclosure first aspect provides a kind of carbazole compound, which has as shown in following formula (1)
Structure:
Wherein, R1、R2、R3And R4In at least one be group shown in formula (2), remaining is selected from hydrogen atom, C1~C10Alkane
Base, substituted or unsubstituted C6~C30Aryl and substituted or unsubstituted C3~C30At least one of heteroaryl；R1’、R2’、R3’
And R4’In at least one be group shown in formula (2), remaining is selected from hydrogen atom, C1~C10Alkyl, substituted or unsubstituted C6~
C30Aryl and substituted or unsubstituted C3~C30At least one of heteroaryl；L is selected from singly-bound, substituted or unsubstituted C6~C30
Arlydene, substituted or unsubstituted C3~C30Inferior heteroaryl；Ar is the group that Hammett value is positive；
Wherein, * is connection site, and X is C atom or Si atom, R5、R6、R7、R8、R5’、R6’、R7’、R8’、R9、R10、R11、
R12And R13It is each independently selected from hydrogen atom, C1~C10Alkyl, substituted or unsubstituted C6~C30Aryl and substituted or unsubstituted
C3~C30At least one of heteroaryl；
The substituted C6~C30Arlydene, substituted C3~C30Inferior heteroaryl, substituted C6~C30Aryl, substituted C3
~C30Substituent group in heteroaryl is each independently selected from halogen, cyano, C1~C10Alkyl, C3~C10Naphthenic base, C2~
C6Alkenyl, C1~C6Alkoxy, C1~C6Thio alkoxy, C6~C30Aryl and C3~C30Heteroaryl at least
It is a kind of.
Wherein, the Hammett value, also known as Hammett substituent constant, be acquired according to Hammett's rule, to specific
The characterization of group charge affinity is the measurement of electron-withdrawing group (positive Hammett value) or electron donating group (negative Hammett value).
In Thomas H.Lowry and Katheleen Schueller Richardson, " Mechanism and Theory In
Organic Chemistry ', New York is described in more detail Hammett equation in page 1987,143-151, draws work herein and join
It examines.
Hammett's rule be in order to quantitatively illustrate substituent group to the reaction of benzene derivative or the influence of balance and by
The rule of thumb that L.P.Hammet is proposed in nineteen thirty-five still approves its extensive validity now.The Kazakhstan that Hammett's rule acquires
The special constant of rice has contraposition-Hammett substituent constant σ p value and meta position-Hammett substituent constant σ m value, these values can be very
It is found in mostly common books.Such as at J.A.Dean volume, " Lange ' sHandbookofChemistry " the 12nd edition, 1979
(McGraw-Hill) or " chemical field " supplementary issue, No. 122, page 96~103, (Nan Guangtang), Chem.Rev. in 1979,1991
Year, volume 91, be documented in page 165~195 etc..The group that Hammett value is positive described in the disclosure refers to σ p and/or σ
M is the substituent group of positive value.
It should be noted that, although Ar is defined or is illustrated by Hammett value in the present invention, but Ar is not only
It is limited to the substituent group with document given value found in above-mentioned books, it is expected that understanding are as follows: even if not remembering comprising the value also
It carries in the literature but includes substituent group in the range when measuring based on Hammett's rule.
When Hammett value is negative value, expression substituent group is that electron donating property substituent group indicates to take when Hammett constant is positive value
Dai Jiwei electron-attracting substituent, in above-mentioned formula (1), Ar is the group that Hammett value is positive number, preferably Hammett value be 0~
When 1, the electron-withdrawing of Ar is suitable for that the electron transport ability that can increase substantially entire molecule is connect with carbazole group, should
The case where Hammett value is more preferably 0.2~0.8.
Further, Ar can be selected from substituted or unsubstituted triazine radical, substituted or unsubstituted pyrimidine radicals, substitution or not
Substituted pyridyl group, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinazolyl, substituted or unsubstituted isoquinoline
Oxazoline base, substituted or unsubstituted pyrazinyl, cyano-phenyl, dicyano phenyl, carbonyl phenyl, xanthene ketone group, benzene sulfuryl, three
One of methyl fluoride and nitro.
Wherein, the substituted triazine radical, substituted pyrimidine radicals, substituted pyridyl group, substituted quinoxalinyl, replace
Substituent group in pyrazinyl, substituted quinazolyl and substituted different quinazolyl can be each independently selected from halogen, cyano,
C1~C10Alkyl, C3~C10Naphthenic base, C2~C6Alkenyl, C1~C6Alkoxy, C1~C6Thio alkoxy, C6~
C30Aryl and C3~C30At least one of heteroaryl；Halogen can be at least one of-F ,-Cl ,-Br ,-I, C1~
C4Alkyl be preferably at least one of methyl, ethyl, n-propyl, isopropyl, normal-butyl, isobutyl group and tert-butyl, C1~C4
Alkoxy be preferably at least one of methoxyl group, ethyoxyl, positive propoxy, isopropoxy, n-butoxy, C3~C6Ring
Alkyl is preferably cyclopenta or cyclohexyl；It is highly preferred that substituent group in above-mentioned group can for cyano, phenyl, xenyl and
At least one of pyridyl group.Wherein, substituent group can also be further substituted, for example, substituent group be phenyl or pyridyl group when,
Phenyl or pyridyl group can be further by cyano, halogen, C1~C4The groups such as alkyl replace, preferred substituent group is further
Group after substitution can be aminomethyl phenyl, tert-butyl-phenyl.The number of substituent group is unlimited, and preferably 1~3.
In the carbazole compound of the disclosure, fluorenes, thiophene are coughed up and carbazole group all has preferable cavity transmission ability, when
After introducing the group that the Hammetts values such as pyrimidine, 1,3,5-triazines, carbonyl are positive, the electron-transport energy of molecule can be increased substantially
Power can expand the recombination region of its carrier, be effectively reduced effect when using in the luminescent layer of organic electroluminescence device
Rate is roll-offed；Fluorenes, thiophene are coughed up and carbazole group triplet with higher, can be as three kinds of luminescent materials of red, green, blue
Material of main part uses, in addition, the energy gap of the series compound is also relatively narrow, is conducive to the injection of carrier, can be effectively reduced
The cut-in voltage of device；The carbazole compound of the disclosure is connected with fluorenes/thiophene on carbazole and coughs up structure simultaneously, and entire molecule is presented
Biggish rigid distortion structure out is quenched caused by capable of being effectively reduced because of aggregation, can improve organic electroluminescence device
Luminous efficiency.
According to the disclosure, substituted C6~C30Arlydene, substituted C3~C30Inferior heteroaryl, substituted C6~C30Aryl,
Substituted C3~C30Heteroaryl, substituted pyrimidine radicals, substituted pyridyl group, substituted quinoxalinyl, replaces substituted triazine radical
Pyrazinyl, the substituent group in substituted quinazolyl and substituted different quinazolyl be preferably halogen, cyano, C1~C4Alkane
Base, C3~C6Naphthenic base, C1~C4At least one of alkoxy, phenyl, xenyl and pyridyl group；Wherein, halogen can be with
For at least one of-F ,-Cl ,-Br ,-I, C1~C4Alkyl be preferably methyl, ethyl, n-propyl, isopropyl, normal-butyl,
At least one of isobutyl group and tert-butyl, C1~C4Alkoxy be preferably methoxyl group, ethyoxyl, positive propoxy, isopropyl oxygen
At least one of base, n-butoxy, C3~C6Naphthenic base be preferably cyclopenta or cyclohexyl.Wherein, substituent group can be into one
Step be substituted, such as substituent group be phenyl or pyridyl group when, phenyl or pyridyl group can be further by cyano, halogen, C1~C4's
The groups such as alkyl replace.
According to the disclosure, C6~C30Aryl be it is well-known to those skilled in the art, that is, have 6~30 skeleton carbon originals
Son aryl, preferably with 6~15 backbone carbon atoms aryl, such as can for selected from phenyl, xenyl, terphenyl,
Naphthalene, anthryl, phenanthryl, indenyl, fluorenyl, benzo fluorenyl, 9,9 '-dialkyl fluorenyls, 9,9 '-spiral shell, two fluorenyl, indeno fluorenyl, fluoranthene
Base, triphenylene, pyrenyl, base,Base and aphthacene baseAt least one of base；Wherein, xenyl may include being selected from
2- xenyl, 3- xenyl and 4- xenyl；Terphenyl may include p- terphenyl -4- base, p- terphenyl -3-
In base, p- terphenyl -2- base, m- terphenyl -4- base, m- terphenyl -3- base and m- terphenyl -2- base extremely
Few one kind, naphthalene may include 1- naphthalene and/or 2- naphthalene, anthryl may include in 1- anthryl, 2- anthryl and 9- anthryl extremely
Few one kind, pyrenyl may include selected from least one of 1- pyrenyl, 2- pyrenyl and 4- pyrenyl.According to the disclosure, C6~C30It is sub-
Aryl be it is well-known to those skilled in the art, i.e., with 6~30 backbone carbon atoms arlydene, it is possible to further for
By the C of mentioned kind6~C30Aryl lose the arlydene of hydrogen atom formation, preferably phenylene.
According to the disclosure, heteroaryl refers to at least one hetero atom and with the monocycle of certain amount ring skeleton atom
Or polycyclic aromatic group, hetero atom may include one or more hetero atoms selected from B, N, O, S, P (=O), Si and P；It is preferred that
Ground, hetero atom may include one or more hetero atoms for being selected from O, S and N.C3~C30Heteroaryl has 3~30 skeleton carbon originals
Son preferably has 3~15 backbone carbon atoms, such as can be for selected from thienyl, furyl, dibenzofuran group, azepine two
Benzofuranyl, azepine dibenzothiophene, dibenzothiophene, dibenzo selenophen base, carbazyl, carboline base, pyrrole radicals, miaow
Oxazolyl, benzimidazolyl, indyl, pyridyl group, oxazolyl, oxadiazoles base, benzoxazolyl, triazine radical, pyrimidine radicals, quinazoline
At least one of base, quinoxalinyl, naphthyridines base, phenazinyl, ferrosin base, benzimidazolyl and indolocarbazole base；It is preferred that
For at least one of pyridyl group, bipyridyl, phenylpyridyl.According to the disclosure, C3~C30Inferior heteroaryl is this field skill
Known to art personnel, i.e., with the inferior heteroaryl of 3~30 backbone carbon atoms, it is possible to further for by mentioned kind
C3~C30Heteroaryl loses the inferior heteroaryl of hydrogen atom formation, preferably phenylene, sub-pyridyl group.
According to the disclosure, C1~C10Alkyl be it is well-known to those skilled in the art, i.e., with 1~10 carbon atom
Aliphatic alkyl, can in methyl, ethyl, propyl, butyl, amyl, hexyl, heptyl, octyl, nonyl and decyl extremely
Few one kind, wherein alkyl can be direct-connected alkyl or the alkyl with branch, further preferably methyl, ethyl, n-propyl, different
In propyl, normal-butyl, isobutyl group, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl and positive decyl at least
It is a kind of.
According to the disclosure, C1~C10Alkoxy be it is well-known to those skilled in the art, that is, have 1~10 carbon atom
Alkoxy, can be methoxyl group, ethyoxyl, positive propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, just
At least one of amoxy, positive hexyloxy, positive oxygroup in heptan, n-octyloxy, positive nonyl epoxide and n-decyloxy, preferably methoxy
In base, ethyoxyl, positive propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, n-pentyloxy and positive hexyloxy
It is at least one.
According to the disclosure, the C3~C10Naphthenic base be it is well-known to those skilled in the art, that is, have 3~10 carbon
The naphthenic base of atom, preferably cyclopenta or cyclohexyl.
According to the disclosure, fluorenyl/thiophene is respectively connected on two phenyl ring of carbazole group in carbazole compound and coughs up base
In embodiment, the position of substitution of group shown in formula (2) (i.e. fluorenyl/thiophene coughs up base group) is not particularly limited, carbazole group
The position of group shown in linking (2) can be corresponding or be not correspond on two phenyl ring, both preferably corresponding, i.e. formula (2)
Shown group symmetrically replaces on two phenyl ring of carbazyl；Further, group shown in formula (2) can be in R2And R2’Or R3With
R3’Replace, to reduce steric hindrance convenient for preparation, specifically for example, R2And R2’It can be respectively group shown in formula (2), R1、R3、R4、
R1’、R3’And R4’It is each independently selected from hydrogen atom, C1~C10Alkyl, substituted or unsubstituted C6~C30Aryl is with substitution or not
Substituted C3~C30At least one of heteroaryl, preferably at least one of hydrogen atom or methyl；Further preferred R2With
R2’It can be identical；Alternatively, R3And R3’It can be respectively group shown in formula (2), R1、R2、R4、R1’、R2’And R4’It selects each independently
From hydrogen atom, C1~C10Alkyl, substituted or unsubstituted C6~C30Aryl and substituted or unsubstituted C3~C30In heteroaryl
At least one, preferably at least one of hydrogen atom or methyl；Further preferred R3And R3’It can be identical.
It is further preferred that R2And R2’It can be respectively group shown in formula (2), R1、R3、R4、R1’、R3’And R4’Can be
Hydrogen atom；Alternatively, R3And R3’It can be respectively group shown in formula (2), R1、R2、R4、R1’、R2’And R4’It can be hydrogen atom.Its
In, R2And R2’Respectively group shown in formula (2) when, R2And R2’Can be identical or different, it is preferably identical；R3And R3’Respectively formula
(2) shown in when group, R2And R2’Can be identical or different, it is preferably identical.
According to the disclosure, L is preferably singly-bound, substituted or unsubstituted C6~C15Arlydene, substituted or unsubstituted C3
~C15Inferior heteroaryl, further preferably in singly-bound, phenylene, sub-pyridyl group, methylphenylene and dimethylphenylene
It is a kind of；Wherein phenylene may include one of 1,2- phenylene, 1,3- phenylene, 1,4- phenylene.
According to the disclosure, Ar can preferably be selected from one of structure shown in following formula (3)~formula (11):
Wherein, * is connection site, and R ' and R " can be each independently selected from hydrogen atom, C1~C10Alkyl, substitution do not take
The C in generation6~C30Aryl and substituted or unsubstituted C3~C30At least one of heteroaryl, preferably hydrogen atom, C1~C6Alkane
Base, substituted or unsubstituted C6~C15Aryl, further preferably hydrogen atom, methyl, tert-butyl, phenyl, in xenyl extremely
Few one kind.
According to the disclosure, in the structure shown in formula (2), it is preferable that R5、R6、R7、R8、R5’、R6’、R7’、R8’、R9、R10、
R11、R12And R13It can be hydrogen atom.
According to the disclosure, the carbazole compound can be selected from one of following structural formula:
Disclosure second aspect provides carbazole compound described in disclosure first aspect and is preparing organic electroluminescent
Application in device.
According to the disclosure, the carbazole compound has preferable electronic transmission performance and higher triplet,
It may be used as the luminescent layer material of main part and/or guest materials of the organic electroluminescence device.
The disclosure third aspect provides a kind of organic electroluminescence device, including substrate, anode layer, cathode layer, Yi Jijie
At least one layer of organic function layer between anode layer and cathode layer, the organic function layer include hole injection layer, hole biography
Defeated layer, organic luminous layer, electron transfer layer and electron injecting layer, the hole injection layer, hole transmission layer, organic light emission
Layer, electron transfer layer and electron injecting layer are sequentially formed on the anode layer, and the organic function layer contains first party
Carbazole compound described in face preferably comprises at least one of compound M1~M108.
It is further preferred that the material of main part and/or guest materials of the organic luminous layer contain described in first aspect
Carbazole compound preferably comprises at least one of compound M1~M108.
Excellent properties of the organic electroluminescence device of the disclosure based on disclosure compound can reduce device and open electricity
Pressure improves luminous efficiency, reduces efficiency roll-off.
Brief description is carried out to the synthetic method of the compounds of this invention below.
Representative synthesis path:
Wherein, Ar and X has definition same as described above.Unless otherwise indicated, the synthetic method of the disclosure it is raw materials used,
Intermediate is all the raw produce being obtained through commercial channels.Solvent for use and reagent in the disclosure, such as methylene chloride, petroleum
Ether, tetrahydrofuran, n,N-dimethylacetamide, anhydrous magnesium sulfate, boron trifluoride ether, carbazole, is changed fluorobenzoic boric acid etc. ethyl alcohol
Reagent is learned, can be bought from domestic chemical products market, such as purchase is finished from Chinese medicines group Reagent Company, TCI company, Shanghai
Obtain pharmaceuticals, lark prestige Reagent Company etc..In addition, those skilled in the art can also be synthesized by known method.
The analysis detection of intermediate and compound in the present invention uses ABSCIEX mass spectrograph (4000QTRAP) He Saimo
Fly organic element analyzer.
Above two synthetic routes are illustrated below with reference to synthetic example 1~10.
Synthetic example 1: the synthesis of compound M1
The synthesis of intermediate A -1:
It takes a 500mL bottle with two necks newly dried, under nitrogen protection, sequentially adds 8.8g (34.1mmol) 9- phenyl -9- fluorenes
The dry methylene chloride of 200mL is added in alcohol, 1.9g (11.4mmol) carbazole later.After 1h is stirred at room temperature, it is molten that 30mL is added dropwise
There is the mixed solution of 4.8g (34.1mmol) boron trifluoride etherate.20h is persistently stirred after being added dropwise.Reaction stops
Afterwards, it is first slowly added to 50mL dehydrated alcohol, 50mL water is slow added into and is quenched.Reaction system is extracted with methylene chloride,
It is dried after merging organic phase with anhydrous magnesium sulfate, silica gel column chromatography separation is carried out after concentration, petroleum ether: methylene chloride=
10:1 is eluted, and obtains beige solid A-1,5.3g, yield 72% after eluent concentration.Mass spectral analysis determine molecule from
Protonatomic mass are as follows: 647.51 (calculated values are as follows: 647.26)；Theoretical elemental content (%) C50H33N:C, 92.70；H, 5.13；N,
2.16.Survey constituent content (%): C, 92.72；H, 5.15；N, 2.16.Above-mentioned analysis the result shows that, the product of acquisition is estimated
Product.
The synthesis of intermediate M1-1: a dry 250mL bottle with two necks is taken, 3.1g (22mmol) 4- fluorobenzene boron is sequentially added
Acid, chloro- 4, the 6- diphenyl -1,3,5-triazines of 5.3g (20mmol) 2- and 3.0g (22mmol) Anhydrous potassium carbonate, nitrogen displacement
After three times, 288mg (0.25mmol) tetra-triphenylphosphine palladium and 11mL water and 150mL tetrahydrofuran is added.Under nitrogen atmosphere
It is heated to reflux sustained response 10h.After reaction stops, vacuum distillation removes the solvent in reaction system, obtains a large amount of brown colors
Solid.Crude product is dissolved with 200mL methylene chloride, organic phase is merged after massive laundering and is dried with anhydrous magnesium sulfate,
Silica gel column chromatography separation is carried out after concentration, petroleum ether: methylene chloride=8:1 is eluted, and it is solid to obtain white after eluent concentration
Body M1-1,6.1g, yield 93%.The molecular ion quality that mass spectral analysis determines are as follows: 327.21 (calculated values are as follows: 327.12)；Reason
Argument cellulose content (%) C21H14FN3:C, 77.05；H, 4.31；F, 5.80；N, 12.84.Constituent content (%): C is surveyed,
77.06；H, 4.21；F, 5.85；N, 12.88.Above-mentioned analysis the result shows that, the product of acquisition is estimated product.
The synthesis of compound M1: a dry 250mL single port bottle is taken, 6.5g (10mmol) A-1,3.3g is sequentially added
(10mmol) M1-1 and 4.9g (15mmol) cesium carbonate, DMF (N, N- the dimethyl formyl after 120mL drying is added later
Amine).After nitrogen displacement three times, 150 DEG C of sustained response 20h are heated under nitrogen atmosphere.After reaction stops, vacuum distillation is removed
DMF in reaction system obtains a large amount of yellow-brown solids.Crude product is dissolved with 500mL methylene chloride, is merged after massive laundering
Organic phase is simultaneously dried with anhydrous magnesium sulfate, after concentration carry out silica gel column chromatography separation, petroleum ether: methylene chloride=5:1 into
Row elution obtains white solid M1,7.6g, yield 84% after eluent concentration.The molecular ion quality that mass spectral analysis determines are as follows:
954.33 (calculated values are as follows: 954.37)；Theoretical elemental content (%) C71H46N4: C, 89.28；H, 4.85；N, 5.87.Survey element
Content (%): C, 89.26；H, 4.81；N, 5.85.Above-mentioned analysis the result shows that, the product of acquisition is estimated product.
Synthetic example 2: the synthesis of compound M2
The synthesis of intermediate A -2:
Using the synthetic method of intermediate A -1, difference is to replace with carbazole into 1, the 8- dimethyl -9-H- click of equivalent
Azoles obtains beige solid A-2,5.4g, yield 75%.The molecular ion quality that mass spectral analysis determines are as follows: 675.22 (calculated values
Are as follows: 675.29)；Theoretical elemental content (%) C52H37N:C, 92.41；H, 5.52；N, 2.07.Constituent content (%): C is surveyed,
92.42；H, 5.48；N, 2.11,.Above-mentioned analysis the result shows that, the product of acquisition is estimated product.
The synthesis of compound M2: using the synthetic method of compound M1, difference is intermediate A -1 replacing with equivalent
Intermediate A -2, obtain beige solid A-2,7.2g, yield 83%.The molecular ion quality that mass spectral analysis determines are as follows:
982.38 (calculated values are as follows: 982.40)；Theoretical elemental content (%) C73H50N4: C, 89.18；H, 5.13；N, 5.70.Survey element
Content (%): C, 89.21；H, 4.97；N, 5.16.Above-mentioned analysis the result shows that, the product of acquisition is estimated product.
Synthetic example 3: the synthesis of compound M3
Using the synthetic method of compound M1, difference, which is to replace with chloro- 4, the 6- diphenyl -1,3,5-triazines of 2-, etc. works as
Chloro- 4, the 6- diphenylpyrimidin of the 2- of amount, obtains beige solid M3,7.2g, yield 83%.The molecular ion that mass spectral analysis determines
Quality are as follows: 953.22 (calculated values are as follows: 953.38)；Theoretical elemental content (%) C72H47N3: C, 90.63；H, 4.97；N, 4.40.
Survey constituent content (%): C, 90.52；H, 4.87；N, 5.01.Above-mentioned analysis the result shows that, the product of acquisition is estimated production
Product.
Synthetic example 4: the synthesis of compound M4
Using the synthetic method of compound M3, difference is to replace with intermediate A -1 into the intermediate A -2 of equivalent, obtain
To beige solid M4,6.8g, yield 67%.The molecular ion quality that mass spectral analysis determines are as follows: 981.20 (calculated value are as follows:
981.41)；Theoretical elemental content (%) C74H51N3: C, 90.49；H, 5.23；N, 4.28.Constituent content (%): C is surveyed,
90.51；H, 5.20；N, 4.21.Above-mentioned analysis the result shows that, the product of acquisition is estimated product.
Synthetic example 5: the synthesis of compound M7
Using the synthetic method of compound M1, difference is to replace with intermediate M1-1 into the 4- fluorine hexichol first of equivalent
Ketone obtains beige solid M7,7.3g, yield 78%.The molecular ion quality that mass spectral analysis determines are as follows: 827.31 (calculated values
Are as follows: 827.32)；Theoretical elemental content (%) C63H41NO:C, 91.39；H, 4.99；N, 1.69；O, 1.93.Survey constituent content
(%): C, 91.36；H, 5.02；N, 1.67；O, 1.96.Above-mentioned analysis the result shows that, the product of acquisition is estimated product.
Synthetic example 6: the synthesis of compound M8
Using the synthetic method of compound M7, difference is to replace with intermediate A -1 into the intermediate A -2 of equivalent, obtain
To white solid M8,6.4g, yield 63%.The molecular ion quality that mass spectral analysis determines are as follows: 855.31 (calculated value are as follows:
855.35)；Theoretical elemental content (%) C65H45NO:C, 91.20；H, 5.30；N, 1.64；O, 1.87.Survey constituent content
(%): C, 91.30；H, 5.26；N, 1.67；O, 1.90.Above-mentioned analysis the result shows that, the product of acquisition is estimated product.
Synthetic example 7: the synthesis of compound M9
Using the synthetic method of compound M7, difference is to replace with 4- fluorine benzophenone into the 4- fluorine hexichol of equivalent
Sulfone obtains beige solid M9,7.5g, yield 78%.The molecular ion quality that mass spectral analysis determines are as follows: 863.31 (calculated values
Are as follows: 863.29)；Theoretical elemental content (%) C62H41NO2S:C, 86.18；H, 4.78；N, 1.62；O, 3.70；S, 3.71.Actual measurement
Constituent content (%): C, 86.16；H, 4.77；N, 1.65；O, 3.72；S, 3.71.Above-mentioned analysis the result shows that, the product of acquisition
For estimated product.
Synthetic example 8: the synthesis of compound M10
Using the synthetic method of compound M9, difference is to replace with intermediate A -1 into the intermediate A -2 of equivalent, obtain
To white solid 6.1g, yield 66%.The molecular ion quality that mass spectral analysis determines are as follows: 891.29 (calculated values are as follows: 891.32)；
Theoretical elemental content (%) C64H45NO2S:C, 86.17；H, 5.08；N, 1.57；O, 3.59；S, 3.59.Survey constituent content
(%): C, 86.17；H, 5.10；N, 1.55；O, 3.62；S, 3.54.Above-mentioned analysis the result shows that, the product of acquisition is estimated
Product.
Synthetic example 9: the synthesis of compound M47
Using the synthetic method of compound M1, difference is to replace with 4- fluorobenzoic boric acid into the 3- fluorobenzoic boric acid of equivalent,
Obtain white solid 7.2g, yield 85%.The molecular ion quality that mass spectral analysis determines are as follows: 954.21 (calculated value are as follows:
954.37)；Theoretical elemental content (%) C71H46N4: C, 89.28；H, 4.85；N, 5.87.Constituent content (%): C is surveyed,
89.28；H, 4.82；N, 5.86.Above-mentioned analysis the result shows that, the product of acquisition is estimated product.
Synthetic example 10: the synthesis of compound M48
Using the synthetic method of compound M47, difference is to replace with intermediate A -1 into the intermediate A -2 of equivalent, obtain
To white solid 6.2g, yield 83%.The molecular ion quality that mass spectral analysis determines are as follows: 982.38 (calculated values are as follows: 982.40)；
Theoretical elemental content (%) C73H50N4:C, 89.18；H, 5.13；N, 5.70.Survey constituent content (%): C, 89.21；H,
4.97；N, 5.56.Above-mentioned analysis the result shows that, the product of acquisition is estimated product.
The luminescent layer and organic electroluminescence device of organic electroluminescence device of the invention are illustrated below.
The luminescent layer of organic electroluminescence device of the invention, including material of main part and dyestuff.The compound of the present invention was both
Can be used as material of main part come using, can also be used as dyestuff come using.
Organic electroluminescence device of the invention, including substrate, and sequentially form anode layer on the substrate, more
A light emitting functional layer and cathode layer；
The light emitting functional layer includes hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, the sky
Cave implanted layer is formed on the anode layer, and the hole transmission layer is formed on the hole injection layer, described
Cathode layer is formed on the electron transfer layer, is luminous between the hole transmission layer and the electron transfer layer
Layer；The luminescent layer is the luminescent layer of the organic electroluminescence device of aforementioned present invention.
Specifically, anode material can use indium tin oxygen (ITO), indium zinc oxygen (IZO), stannic oxide (SnO2), zinc oxide
(ZnO) etc. transparent conductive materials are also possible to the metal materials such as silver and its alloy, aluminium and its alloy, and being also possible to PEDOT etc. has
The multilayered structure of machine conductive material and above-mentioned material.
Hole injection layer material can include but is not limited at least one in following enumerated compound HI-1~HI-3
Kind:
Hole transport layer material can include but is not limited at least one in following enumerated compound HT-1~HT-33
Kind:
Phosphorescent light body material can include but is not limited in following enumerated compound GPH-44~GPH-80 at least
It is a kind of:
Fluorescent dye can include but is not limited to following enumerated at least one of compound TDE-1~TDE-39:
Phosphorescent coloring can include but is not limited to following enumerated at least one of compound PD-1~PD-17:
Electron transport layer materials can include but is not limited at least one in following enumerated compound ET-1~ET-62
Kind:
It can also include the electron injecting layer between electron transfer layer and cathode, electron injecting layer material packet in device
It includes but is not limited to the following one or more combinations enumerated:
LiQ,LiF,NaCl,CsF,Li2O,Cs2CO3,BaO,Na,Li,Ca。
Cathode is metals, metal mixture, the oxide such as magnesium silver mixture, LiF/Al, ITO.
Device embodiments 1: using the compound M1 of the disclosure as thermal activation delayed fluorescence type organic electroluminescence device
Material of main part.
Device architecture is as follows:
ITO (150nm)/HI-2 (10nm)/HT-2 (40nm)/M1:TDE-7 (30nm, 5%wt)/ET-59 (25nm)/LiF
(0.5nm)/Al(150nm)。
Organic electroluminescence device preparation process is as follows: will be coated with the glass plate of ITO (thickness 150nm) transparency conducting layer
It is ultrasonically treated in commercial detergent, rinses in deionized water, in acetone: ultrasonic oil removing in alcohol mixed solvent, in cleaning
It is baked under environment and completely removes moisture content, with ultraviolet light and ozone clean, and with low energy cation beam bombarded surface；
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 × 10-5~1 × 10-4Pa, above-mentioned
Vacuum evaporation HI-2 and HT-2 is respectively as hole injection layer and hole transmission layer on anode tunic, evaporation rate 0.1nm/s,
It is respectively 10nm and 40nm that film thickness, which is deposited,；
Hair of the vacuum evaporation " M1:TDE7 (30nm, 5%wt) " as organic electroluminescence device on hole transmission layer
Photosphere, evaporation rate 0.1nm/s, vapor deposition total film thickness are 30nm；Wherein " 5%wt " refers to the doping ratio of blue light dyestuff, i.e.,
The weight part ratio of material of main part and TDE7 are 95:5.
Electron transfer layer of the vacuum evaporation ET59 as organic electroluminescence device, evaporation rate are on luminescent layer
0.1nm/s, vapor deposition total film thickness are 20nm；
The LiF of vacuum evaporation 0.5nm is as the Al of electron injecting layer and 150nm as cathode on the electron transport layer.
Device embodiments 2~6: using the compound of the disclosure as thermal activation delayed fluorescence type organic electroluminescence device
Material of main part.
Using the method for device embodiments 1, difference be respectively to replace with material of main part compound M1 M2, M3, M8,
M19 and M47.
Device comparative example 1~2: using other compounds as thermal activation delayed fluorescence type (TADF) organic electroluminescence device
Material of main part.
Using the method for device embodiments 1, difference is material of main part compound M1 replacing with compound GPH- respectively
77 and GPH-81.
Device embodiments 7: using the compound M1 of the disclosure as the material of main part of electrophosphorescence device.
Device architecture is as follows: and ITO (150nm)/HATCN (10nm)/HT-2 (40nm)/M1:PD1 (30nm, 5%
wt)/ET58(25nm)/LiF(0.5nm)/Al(150nm)。
Using the method for device embodiments 1, except that electron transport material changes ET58 by ET59, dyestuff is by TDE7
It is changed to PD1, material of main part is still M1.
Device embodiments 8~12: using the compound of the disclosure as the material of main part of electrophosphorescence device.
Using the method for device embodiments 7, difference be respectively to replace with material of main part compound M1 M2, M3, M8,
M19 and M47.
Device comparative example 3~4: using other compounds as the material of main part of electrophosphorescence device.
Using the method for device embodiments 7, difference is material of main part compound M1 replacing with compound GPH- respectively
77 and GPH-81.
Device embodiments 13: using the compound M1 of the disclosure as fluorescent dye.
Device architecture: ITO (150nm)/HT-32 (20nm)/GPH-79:M1 (30nm, 5wt%)/ET-62 (10nm)/ET-
59(20nm)/LiF(0.5nm)/Al(150nm)。
Organic electroluminescence device preparation process is as follows: will be coated with the glass plate of ITO (thickness 150nm) transparency conducting layer
It is ultrasonically treated in commercial detergent, rinses in deionized water, in acetone: ultrasonic oil removing in alcohol mixed solvent, in cleaning
It is baked under environment and completely removes moisture content, with ultraviolet light and ozone clean, and with low energy cation beam bombarded surface；
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa, above-mentioned
Vacuum evaporation hole transmission layer HT-32 on anode tunic, evaporation rate 0.1nm/s, vapor deposition film thickness are 20nm；
Vacuum evaporation light emitting host material and dyestuff on hole transmission layer, as shining for organic electroluminescence device
Layer, evaporation rate 0.1nm/s, vapor deposition total film thickness are 30nm；
Successively vacuum evaporation electron transfer layer ET-62 and ET-59, evaporation rate are 0.1nm/s on luminescent layer,
It is respectively 10nm and 20nm that film thickness, which is deposited,；
The Al of the LiF of vacuum evaporation 0.5nm on the electron transport layer, 150nm are as electron injecting layer and cathode.
Device embodiments 14~15: using the compound of the disclosure as fluorescent dye.
Using the method for device embodiments 13, difference is dyestuff M1 replacing with M10 and M19 respectively.
Device comparative example 5: using other compounds as fluorescent dye.
Using the method for device embodiments 13, difference is material of main part compound M1 replacing with compound A105.
Following performance measurement is carried out to the organic electroluminescence device prepared by the above process:
Under same brightness, using digital sourcemeter and luminance meter measurement device embodiments 1~15 and device comparative example 1~
The cut-in voltage of the organic electroluminescence device being prepared in 5, maximum brightness simultaneously calculate maximum external quantum efficiency.Specifically
For, voltage is promoted with the rate of 0.1V per second, measurement reaches 1cd/m when the brightness of organic electroluminescence device2When voltage
That is cut-in voltage, while measuring current density at this time and calculating maximum external quantum efficiency according to data such as spectrum；Test
As a result it is listed in Tables 1 and 2 respectively.
Table 1
Table 2
It can see by upper table, when using the compound of the present invention as the main body of TADF type dye and phosphorescent coloring,
Its cut-in voltage, maximum brightness and maximum external quantum efficiency are all promoted, and excellent device performance is shown.Using this hair
The external quantum efficiency of organic electroluminescence device when bright compound is as dyestuff has been over 5%, with conventional fluorescent material
Have compared to cut-in voltage, maximum brightness and maximum external quantum efficiency and promoted significantly, shows excellent device performance.
The preferred embodiment of the disclosure is described in detail above, still, during the disclosure is not limited to the above embodiment
Detail a variety of simple variants can be carried out to the technical solution of the disclosure in the range of the technology design of the disclosure, this
A little simple variants belong to the protection scope of the disclosure.
It is further to note that specific technical features described in the above specific embodiments, in not lance
In the case where shield, it can be combined in any appropriate way.In order to avoid unnecessary repetition, the disclosure to it is various can
No further explanation will be given for the combination of energy.
In addition, any combination can also be carried out between a variety of different embodiments of the disclosure, as long as it is without prejudice to originally
Disclosed thought equally should be considered as disclosure disclosure of that.
Claims (14)
1. a kind of carbazole compound, which is characterized in that the carbazole compound has the structure as shown in following formula (1):
Wherein, R1、R2、R3And R4In at least one be group shown in formula (2), remaining is selected from hydrogen atom, C1~C10Alkyl, substitution
Or unsubstituted C6~C30Aryl and substituted or unsubstituted C3~C30At least one of heteroaryl；R1’、R2’、R3’And R4’In
At least one is group shown in formula (2), remaining is selected from hydrogen atom, C1~C10Alkyl, substituted or unsubstituted C6~C30Aryl
With substituted or unsubstituted C3~C30At least one of heteroaryl；L is selected from singly-bound, substituted or unsubstituted C6~C30Asia virtue
Base, substituted or unsubstituted C3~C30Inferior heteroaryl；Ar is the group that Hammett value is positive；
Wherein, * is connection site, and X is C atom or Si atom, R5、R6、R7、R8、R5’、R6’、R7’、R8’、R9、R10、R11、R12With
R13It is each independently selected from hydrogen atom, C1~C10Alkyl, substituted or unsubstituted C6~C30Aryl and substituted or unsubstituted C3
~C30At least one of heteroaryl；
The substituted C6~C30Arlydene, substituted C3~C30Inferior heteroaryl, substituted C6~C30Aryl, substituted C3~C30
Substituent group in heteroaryl is each independently selected from halogen, cyano, C1~C10Alkyl, C3~C10Naphthenic base, C2~C6Alkene
Base, C1~C6Alkoxy, C1~C6Thio alkoxy, C6~C30Aryl and C3~C30At least one of heteroaryl.
2. carbazole compound according to claim 1, which is characterized in that R2And R2’Respectively group shown in formula (2), R1、
R3、R4、R1’、R3’And R4’It is each independently selected from hydrogen atom, C1~C10Alkyl, substituted or unsubstituted C6~C30Aryl and substitution
Or unsubstituted C3~C30At least one of heteroaryl；Alternatively, R3And R3’Respectively group shown in formula (2), R1、R2、R4、R1’、
R2’And R4’It is each independently selected from hydrogen atom, C1~C10Alkyl, substituted or unsubstituted C6~C30Aryl and substituted or unsubstituted
C3~C30At least one of heteroaryl.
3. carbazole compound according to claim 2, which is characterized in that R2And R2’Respectively group shown in formula (2), R1、
R3、R4、R1’、R3’And R4’It is hydrogen atom；Alternatively, R3And R3’Respectively group shown in formula (2), R1、R2、R4、R1’、R2’And R4’?
For hydrogen atom.
4. carbazole compound according to claim 2 or 3, which is characterized in that R2And R2’Respectively base shown in formula (2)
Group, and R2And R2’It is identical；Alternatively, R3And R3’Respectively group shown in formula (2), and R3And R3’It is identical.
5. carbazole compound according to any one of claims 1 to 3, it is characterised in that Ar, which is selected from, to be replaced or do not take
The triazine radical in generation, substituted or unsubstituted pyrimidine radicals, substituted or unsubstituted pyridyl group, substituted or unsubstituted quinoxalinyl,
Substituted or unsubstituted quinazolyl, substituted or unsubstituted different quinazolyl, substituted or unsubstituted pyrazinyl, cyano benzene
One of base, dicyano phenyl, carbonyl phenyl, xanthene ketone group, benzene sulfuryl, trifluoromethyl and nitro；
The substituted triazine radical, substituted pyridyl group, substituted quinoxalinyl, substituted pyrazinyl, takes substituted pyrimidine radicals
Substituent group in the quinazolyl in generation and substituted different quinazolyl is each independently selected from halogen, cyano, C1~C10Alkyl,
C3~C10Naphthenic base, C2~C6Alkenyl, C1~C6Alkoxy, C1~C6Thio alkoxy, C6~C30Aryl and C3
~C30At least one of heteroaryl.
6. carbazole compound according to any one of claims 1 to 3, which is characterized in that the C6~C30Aryl
For selected from phenyl, xenyl, terphenyl, naphthalene, anthryl, phenanthryl, indenyl, fluorenyl, benzo fluorenyl, 9,9 '-dialkyl fluorenyls,
9,9 '-spiral shell, two fluorenyl, indeno fluorenyl, fluoranthene base, triphenylene, pyrenyl, base,Base and aphthacene baseIn base at least
It is a kind of；
The C3~C30Heteroaryl is selected from thienyl, furyl, dibenzofuran group, azepine dibenzofuran group, azepine two
Benzothienyl, dibenzothiophene, dibenzo selenophen base, carbazyl, carboline base, pyrrole radicals, imidazole radicals, benzimidazolyl,
Indyl, pyridyl group, oxazolyl, oxadiazoles base, benzoxazolyl, triazine radical, pyrimidine radicals, quinazolyl, quinoxalinyl, naphthyridines
At least one of base, phenazinyl, ferrosin base, benzimidazolyl and indolocarbazole base；
The C1~C10Alkyl be selected from methyl, ethyl, n-propyl, isopropyl, normal-butyl, isobutyl group, tert-butyl, n-pentyl,
At least one of n-hexyl, n-heptyl, n-octyl, n-nonyl and positive decyl；
The C1~C10Alkoxy be selected from methoxyl group, ethyoxyl, positive propoxy, isopropoxy, n-butoxy, isobutoxy,
At least one of tert-butoxy, n-pentyloxy, positive hexyloxy, positive oxygroup in heptan, n-octyloxy, positive nonyl epoxide and n-decyloxy.
7. carbazole compound according to any one of claims 1 to 3, which is characterized in that L is selected from singly-bound, sub- benzene
One of base, sub-pyridyl group, methylphenylene and dimethylphenylene.
8. carbazole compound according to any one of claims 1 to 3, which is characterized in that Ar be selected from following formula (3)~
One of structure shown in formula (11):
Wherein, * is connection site, and R ' and R " are each independently selected from hydrogen atom, C1~C10Alkyl, substituted or unsubstituted C6~
C30Aryl and substituted or unsubstituted C3~C30At least one of heteroaryl.
9. carbazole compound according to any one of claims 1 to 3, which is characterized in that in the formula (2), R5、
R6、R7、R8、R5’、R6’、R7’、R8’、R9、R10、R11、R12And R13It is hydrogen atom.
10. carbazole compound according to any one of claims 1 to 3, which is characterized in that the carbazoles chemical combination
Object is selected from one of following structural formula:
11. carbazole compound described in any one of claim 1~10 is preparing answering in organic electroluminescence device
With.
12. application according to claim 11, which is characterized in that the carbazole compound is sent out as the organic electroluminescence
The luminescent layer material of main part and/or guest materials of optical device.
13. a kind of organic electroluminescence device, including substrate, anode layer, cathode layer and between anode layer and cathode layer
At least one layer of organic function layer, the organic function layer includes hole injection layer, hole transmission layer, organic luminous layer, electronics
Transport layer and electron injecting layer, which is characterized in that the organic function layer contains according to any one of claims 1 to 10
Carbazole compound.
14. organic electroluminescence device according to claim 13, which is characterized in that the main body material of the organic luminous layer
Material and/or guest materials contain the carbazole compound.
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| CN114249715A (en) * | 2020-09-25 | 2022-03-29 | 江苏三月科技股份有限公司 | Organic compound containing xanthone and triazine structure and application thereof |
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